[ CAS No. 324028-95-7 ] {[proInfo.proName]}

Name: 324028-95-7|6-Chloro-4-methylpyridine-2-carboxylic acid|98%
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SKU: A120219
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Quality Control of [ 324028-95-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 324028-95-7 ]

CAS No. :	324028-95-7	MDL No. :	MFCD09834827
Formula :	C₇H₆ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IDIRHQNTRMGBPJ-UHFFFAOYSA-N
M.W :	171.58	Pubchem ID :	23002381
Synonyms :

Calculated chemistry of [ 324028-95-7 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	41.17
TPSA :	50.19 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.9 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.27
Log Po/w (XLOGP3) :	2.04
Log Po/w (WLOGP) :	1.74
Log Po/w (MLOGP) :	-0.18
Log Po/w (SILICOS-IT) :	1.82
Consensus Log Po/w :	1.34

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.53
Solubility :	0.51 mg/ml ; 0.00297 mol/l
Class :	Soluble
Log S (Ali) :	-2.72
Solubility :	0.325 mg/ml ; 0.0019 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.4
Solubility :	0.688 mg/ml ; 0.00401 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.65

Safety of [ 324028-95-7 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P310-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P362-P501	UN#:	2811
Hazard Statements:	H301-H315-H319-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 324028-95-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 324028-95-7 ]
Downstream synthetic route of [ 324028-95-7 ]

[ 324028-95-7 ] Synthesis Path-Upstream 1~2

1
[ 324028-95-7 ]
[ 3678-62-4 ]

Reference： [1] Journal of the Chemical Society, 1897, vol. 71, p. 653,655

2
[ 209858-74-2 ]
[ 324028-95-7 ]

Reference： [1] Patent: US6610853, 2003, B1,

[ 324028-95-7 ] Synthesis Path-Downstream 1~36

1
[ 324028-95-7 ]
[ 3678-62-4 ]

Reference： [1]Journal of the Chemical Society,1897,vol. 71,p. 653,655

2
[ 209858-74-2 ]
[ 324028-95-7 ]

Yield	Reaction Conditions	Operation in experiment
84.5%	In hydrogenchloride; water;	(3) Synthesis of 6-chloro-4-methyl-2-pyridinecarboxylic acid [Compound (II-8)] 6-Chloro-2-cyano-4-methylpyridine (1.2 g, 7.86 mmol) was heated to 100 C. with stirring in 7 ml of concentrated hydrochloric acid for 30 minutes. The reaction solution was then diluted with 30 ml of water and the resulted precipitate was filtered out, washed water and dried. White solid, m.p.: 127-128 C., yield: 1.13 g, percent yield: 84.5% IR KBr cm-1: 3556, 1701, 1605, 1401, 1314, 1233, 1164.

Reference： [1]Patent: US6610853,2003,B1

3
[ 324028-95-7 ]
[ 108-95-2 ]
[ 324028-94-6 ]

Yield	Reaction Conditions	Operation in experiment
84%	With thionyl chloride; triethylamine;N,N-dimethyl-formamide; In dichloromethane; benzene;	(4) Synthesis of <strong>[324028-95-7]6-chloro-4-methyl-2-pyridinecarboxylic acid</strong> phenyl ester [Compound (IV-8)] 6-Chloro-4-methyl-2-pyridinecarboxylic acid (1 g, 5.83 mmol) was suspended in 15 ml of benzene containing a catalytic amount of DMF. To the suspension was added thionyl chloride (3.46 g, 5.83 mmol), followed by refluxing with heat for 1 hour. An excess amount of thionyl chloride and benzene was then distilled off and the resultant residue was dissolved in 15 ml of dry dichloromethane. The resultant solution was added dropwise to a solution of phenol (0.57 g, 5.831.05 mmol) and triethylamine (0.65 g, 5.831.1 mmol) in 10 ml of dichloromethane under cooling with water. After stirring for 1 hour, the reaction solution was distributed by adding 30 ml of diluted hydrochloric acid. An organic layer was separated and washed with saturated saline solution, and dried with sodium sulfate. The solvent was then distilled off to give a solid. White solid, m.p.: 95-96 C., yield: 1.2 g, percent yield: 84% IR KBr cm-1: 3514, 1758, 1599, 1494, 1293, 1188, 1164, 1095, 867, 732.

Reference： [1]Patent: US6610853,2003,B1

4
[ 324028-95-7 ]
[ 1373273-28-9 ]

Reference： [1]Patent: US2013/289020,2013,A1

5
[ 324028-95-7 ]
C₇H₅Cl₂NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20.0℃; for 3.0h;	6-Chloro-4-methylpyridine-2-carboxylic acid (422 mg, 2.46 mmol) was dissolved in DCM (10 mL) and oxalyl chloride (422 muL, 4.92 mmol) and DMF (100 muL) were added. The reaction mixture was stirred for 3 h, the solvents were removed in vacuo and the residue was azeotroped with DCM. The residue was dissolved in DCM (10 mL), DIPEA (1.63 mL, 9.84 mmol) and aminomethylcyclopropane (427 muL, 4.92 mmol) were added and the reaction mixture was stirred for 1 h. The reaction mixture was diluted with DCM (40 mL), washed with sat aq NaHCO3 (50 mL), 1 M aq HCl (50 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography to give the title compound (494 mg, 69%) as a yellow liquid. LCMS (ES+): 225.5 [MH]+.

Reference： [1]Patent: US2013/289020,2013,A1 .Location in patent: Paragraph 0391

6
[ 324028-95-7 ]
tert-butyl 6-(3-formyl-4-methoxy-2-methylphenyl)-4-methylpyridine-2-carboxylate [ No CAS ]

Reference： [1]Patent: US2014/343052,2014,A1

7
[ 324028-95-7 ]
6-[4-methoxy-2-methyl-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]-4-methyl-N-(methylsulfonyl)pyridine-2-carboxamide [ No CAS ]

Reference： [1]Patent: US2014/343052,2014,A1

8
[ 324028-95-7 ]
6-[4-methoxy-2-methyl-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]-4-methyl-N-(methylsulfonyl)pyridine-2-carboxamide 2-methylpropan-2-amine salt [ No CAS ]

Reference： [1]Patent: US2014/343052,2014,A1

9
[ 324028-95-7 ]
6-[4-methoxy-2-methyl-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]-4-methylpyridine-2-carboxylic acid [ No CAS ]

Reference： [1]Patent: US2014/343052,2014,A1

10
[ 324028-95-7 ]
C₃₆H₄₃NO₆ [ No CAS ]

Reference： [1]Patent: US2014/343052,2014,A1

11
[ 324028-95-7 ]
[ 75-65-0 ]
tert-butyl 6-chloro-4-methylpyridine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With pyridine; p-toluenesulfonyl chloride; at 20.0℃; for 22.0h;	Example 32-1 Tert-butyl 6-chloro-4-methylpyridine-2-carboxylate p-Toluenesulfonyl chloride (1.11 g, 5.83 mmol) was added to a solution of <strong>[324028-95-7]6-chloro-4-methylpyridine-2-carboxylic acid</strong> (0.50 g, 27.6 mmol) as a known compound in tert-butyl alcohol (16.5 ml) and pyridine (2.4 ml) at room temperature, and the mixture thus obtained was then stirred at the same temperature as above for 22 hours. Thereafter, a solution of sodium hydrogen carbonate (1.22 g, 14.6 mmol) in water (33 ml) was added to the resulting solution, and the mixture thus obtained was then stirred. The solvent was distilled away from the reaction solution under reduced pressure. Water was added to the residue thus obtained, and the mixed solution was then extracted with ethyl acetate. The organic layer thus obtained was dried over anhydrous sodium sulfate, and the solvent was then distilled away under reduced pressure to obtain the title compound (0.506 g, yield: 76%). 1H-NMR Spectrum (500 MHz, CDCl3) delta ppm: 7.76 (1H, m), 7.29 (1H, m), 2.41 (3H, m), 1.62 (9H, m).
	With pyridine; p-toluenesulfonyl chloride; at 20.0℃;	tert-Butyl 6-chloro-4-methylpyridine-2-carboxylate 6-Chloro-4-methylpyridine-2-carboxylic acid (2.50 g, 14.6 mmol) was dissolved in pyridine (10 ml) and tert-butanol (50 ml, 520 mmol), and 4-methylbenzenesulphonyl chloride (5.56 g, 29.1 mmol) was added. The reaction mixture was stirred at room temperature overnight and diluted with saturated aqueous sodium hydrogencarbonate solution and cyclohexane/ethyl acetate 90/10. The organic phase was separated off and the aqueous phase was extracted with cyclohexane/ethyl acetate 90/10. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and filtered, and the filtrate was concentrated. 2.89 g (87% purity, 75% of theory) of the title compound were obtained. 1H-NMR (400 MHz, DMSO-d6) delta [ppm]: 1.325 (0.86), 1.340 (0.86), 1.553 (16.00), 7.614 (0.68), 7.830 (0.80).

Reference： [1]Patent: US2014/343052,2014,A1 .Location in patent: Paragraph 0306; 0307
[2]Patent: US2019/160048,2019,A1 .Location in patent: Paragraph 0859-0861

12
[ 324028-95-7 ]
[ 96-41-3 ]
6-(cyclopentyloxy)-4-methylpicolinic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
645 mg	With sodium hydride; In 1,4-dioxane; mineral oil; at 80.0℃; for 24.0h;	To a solution of cyclopentanol (973 mg, 11.3 mmol) in dioxane (10 mL) NaH (407 mg, 10.2 mmol, 60% dispersion in mineral oil) followed by <strong>[324028-95-7]6-chloro-4-methylpicolinic acid</strong> 32 (388 mg, 2.26 mmol) was added. The mixture was stirred at 80C for 24 h before it was acidified by adding 2 N aq. HCl and extracted twice with EA. The organic extracts were dried over Na2SO4, filtered and concentrated to give crude 6-(cyclopentyloxy)-4-methylpicolinic acid (645 mg) as a yellow oil; LC-MS: tR = 0.57 min; [M+1]+ = 222.27. To facilitate purification, the material was dissolved in methanol (15 mL) and TMSCl (2.46 g, 22.6 mmol) was added. The mixture was stirred at 50C for 24 h before it was concentrated. The residue was dissolved sat. aq. NaHCO3 solution and extracted EA. The organic extract was washed again with sat. aq. NaHCO3 solution, dried over Na2SO4, filtered, and concentrated. The crude product was purified by CC on silica gel eluting with heptane:EA 4:1 to give methyl 6-(cyclopentyloxy)-4-methylpicolinate (530 mg, quant.) as a colourless oil

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 115,p. 326 - 341

13
[ 324028-95-7 ]
[ 96-41-3 ]
N-((S)-3-{4-[5-(6-cyclopentyloxy-4-methyl-pyridin-2-yl)-1,2,4-oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 115,p. 326 - 341

14
[ 324028-95-7 ]
(5RS,7RS)-2-[3-fluoro-2-(trifluoromethyl)pyridin-4-yl]methyl}-7-methyl-3-oxo-2,3,5,6,7,8-hexahydro[1,2,4]triazolo[4,3-a]pyridine-5-carboxylic acid [ No CAS ]